Jobs in Daily Fantasy Sports are a SAFE BET w/ Dylan Cooper Senior VP at PrizePicks

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When I was a startup, I was looking for who's going to grind the hardest, who was really passionate about this thing and that formula worked over and over again. More recently, as we've grown from true startup, it's changed now, we are looking more for specialists of knowing sports or knowing this industry isn't good enough anymore. Now, you've got to have some kind of expertise, like you're really good at paid social, like if you're really good at that, and you love sports and you love fantasy sports, that's a huge win. This is the Working Sports Podcast. Here's VP of Content and Engage Learning at workandsports.com, Brian Klaft. Though that fantasy sports has existed since the 1960s, I did not. That was new information to me. I feel like I've been around fantasy sports a long time, and I had no idea that it actually started in the 1960s. I thought Matthew Barry started it in the 80s. That's kind of a joke. Okay, so how did it start? This is stolen straight from research in a New York City hotel room. During a 1962 Raiders Cross Country trip, Wilfred "Bill Wickenbach". That's a rough name. Wilfred Wickenbach. An Oakland California businessman and limited partner in the Oakland Raiders, along with the Raiders Public Relations employee Bill Tunnel, an Oakland Tribune Reporter, Scotty Sterling, developed the rules that would eventually be the basis of modern fantasy football. I find this fascinating. The inaugural league was called the Greater Oakland Professional Pigskin Prognosticators League, G-O-P-P-P-L, which is a terrible name. Nowhere near as good as Brady Gaga, hit me with your press got, Sherlock Mahomes, or Bed Bath and Bijan. If nothing else, over the last 60 years, we've become way more creative. I think we can lean into that a lot. The internet helps out this whole fantasy concept. I think we can all agree it's better to conduct and manage this process online than in some conference room in Oakland. Now, we have 62.5 million Americans playing fantasy sports. 62.5 million Americans put that in perspective for a second. That's nuts. With so many fans playing fantasy sports, that means there is a corresponding need for people to work in fantasy sports, which is our happy place to talk about jobs in the sports industry and opportunities there for all of you. A number of people with fantasy sports jobs increase to 6.8% from 2018 to 2022. The industry is expected to be worth $38.6 billion by 2025. Lots of research went into this intro. I hope you guys are all feeling good about that. A lot of good stuff I'm throwing out here, a lot of nuggets. Wilfred Wickenbock is my personal favorite part of this, though. Fantasy Sports, we know it's successful. There's great opportunities there to work in this field, and there's cool names that you can create. There's also been spin-offs like daily fantasy sports. Why wait for a whole season for a payout to brag with your friends and talk all the trash? When you can win and get payouts daily, which is genius. Today's guest in the Working Sports Podcast is prize picks senior VP of revenue, Dylan Cooper. One of those daily fantasy sports companies are personal favorite here at the Working Sports Podcast, and Dylan enjoys a front row seat to the fantasy sports industry's explosive growth and we're going to get into his journey, his path in fantasy sports. What it's like working on the revenue side and the opportunities that are ahead for daily fantasy sports, so buckle up and enjoy this full episode with Dylan Cooper. Hey Dylan, thanks for joining me on the show today. Nice to meet you. Nice to meet you as well. That's for happening. Yeah, it's a cool conversation to dive into. We've done some of the daily fantasy sports world, and you have a really interesting career path and a lot of that you've experienced, so it's fun to dive into this. I know there's an area that really interests a lot of our audience. So we'll start out with this fantasy sports been around for a long time. A lot of us have spent a lot of our time doing fantasy sports. The daily fantasy sports wrinkle kind of came in around 2007, and that's an angle you've followed for a lot of your career. Why did this part of the sports industry appeal to you? What is drawing you to this industry? And what do you love about it? Yeah, great question. I always grew up just loving sports. I would watch every single bravest game when I was a kid, and I would keep stats on like a piece of paper of every single hit, home runs, out, stolen base. I love that. At every game and at home, I'd watch every same game, and I have those charts of every single stat for an entire season back in like 2005, 2004, when I was a kid. But I took that passion and knowledge that I had for sports and stats, and kind of combined it all over time growing up, I played season-long fantasy first, tried out the ESPN stuff, the CBS, fantasy baseball, fantasy football, fantasy basketball, and it's just so much fun. So I got really into it when I was able to legally play DFS. I found Fandall and DraftKings, which are kind of the two big salary cap games. And I got really, really into it. I was playing every single night. I was on Twitter following all of the main personalities in the industry. I was in the threads and the forums, burger grinders forums, kind of all the really niche things. I was just all in on it. So when opportunity for me to work in this industry popped up, which I can get on later in the show, I jumped at it. It was kind of a dream job, not something I ever thought I would really work in, but worked out really well. And this has always been my major, major passion. Yeah, it's totally aligned. I think so many people that I interview on this show, like they have that background of loving sports wanting to be involved in it, really investing in the time and the passion of it. So it totally makes sense. We had Nigel Eckles on the show a while back who founded Fandall. And just hearing that entrepreneurial spirit and that thought process into launching some of these products is so fascinating to me. And I'm curious about how your early part of your college career lines up with where you are now. So you've been, you went to Georgia Tech, you studied business administration and IT management systems, right? When you first got into college, because I think a lot, this is something our students, our listeners deal with a lot is the vision they have for themselves when they're first starting out. When you first got into college and you were a freshman and you're pursuing these goals, how do you think that all meshes and contributes to where you are, where you are now? Yeah, that's a question I get a lot. So you can legally start playing DFS when you're 18 and a lot of the states on Fandall drafts. So I started playing when I was in high school senior and got really into it as I said college same thing freshman year. And I'm probably not the best example of this. I didn't work as hard as I should have in classes. I like that honesty. I did pretty well in school. I was always able to figure out how to make good grades on tests and on projects without doing too much work. But I was always just very, very focused, kind of later focused on this and not even thinking about it as a job. When I was a freshman, I was like, I'm in Atlanta and a lot of people work at NCR or at Koch or Home Depot, all these kind of big companies in the Atlanta area. That was where my head was. I was consulting or working at one of those companies. And I even applied for internships over the next couple of years at Koch, at those places and even got some of them. But my head was always like fully passionate about DFS and the sports spending space and just kind of that whole ecosystem. And I was spending 12 plus hours a day thinking about that at that time. And that was like not even on purpose. I wasn't trying to angle myself towards any career path. I was just like that bought in and like just what you loved. Yeah. Make it almost as the word to the industry and not to play in the game, but just to like the industry and the whole thing. And I, I just spent so much time doing it. There's a bit of a startup feel to your career too. I think in the sports world, we so often think about the professional sports teams have established for a really long time, long running agencies, you know, Olympic organizations. These are long standing businesses, college athletic programs. These are long standing businesses. But you've got sports grid, daily roto, which was founded in 2013. You joined in 2015. Prize picks founded in October 2017. March 2018 is when you joined. Like you're you're in on these early cusp businesses. What Has that been like being on the ground floor of some of these ventures and really diving into this more of a startup culture? Yeah. Now, I have a lot of friends and a lot of people that ask me, "How do I get in sports? How do I get into this industry?" It's really hard. Like, if you're going to go the route of work at a sports team, work for the Braves or the Falcons or something like, it's doable, but you're going up against the other 10,000 people in Atlanta that are also Lifeline Braves fans and also Lifeline Falcons fans. And it's just going to be harder to get to where you want to go at the end of the day. I didn't learn that the harder. I just kind of like fell into where I fell into because I was just so lazy to focus on this industry with daily roto. So that was a part-time role and it just follows the passion that I had for DFS. I was already playing. I was already following all the news and stuff so right when they launched, they were looking for writers and I was like, "Oh my god, I can get paid to write." I wrote them a long email about all the different things that I had done and I knew and all the stuff. I think it stood out, I think you'd just see the passion. It's hard to fake that. It's hard to fake a true passion point like that. And I ended up writing for them, just writing articles and doing content for them for I don't know, four or five years and it wasn't the highest-paying job of my guy. I was in college and paid maybe $20 an article or an hour or something like that, I don't remember. But I was able to work with some of the smartest people in the sports predictions industry treating my Mike Leone Gailan, a gallon joggy, some really, really sharp guys that I was able to just be in a Slack channel, pick their brain, learn a lot from and eventually help them on certain things that just really, really prepped me for the future and that led me to having a lot of skill that when prize-based came around, I was able to provide a lot of value for them. Yeah, so when you look back at that phase, how did that, we always talk about grabbing experience wherever you can, getting your name out there, building your personal brand. It sounds like when you get into this world, the subset, once you start to get in there and start to know the right people, is that the avenue to start growing within this sphere of the sports industry is a small community and the more you can get known and be present and put a name associated with your content and other activities, is that that key to kind of breaking in there? Yeah, well, I actually didn't create that much of a name for myself. I think I just learned a ton of knowledge. I think the true way, because again, I get hit up all the time, people asking for jobs, asking for this, but when you do have something to bring to them, it's that much more meaningful when you say, like I've had a couple in my career or someone linked in to me and says, I can solve this problem for you. I know you're having this problem hire me to solve this and I've hired those people, I can think of two really major ones on my head that have been the two of the best hires I've made. So it's really about like figuring out a way to create skills that you think are going to be really valuable to solving problems. And this is more of a startup thing, like I have a background in startups, like you said. At a big company, it's completely different, but at a startup, like everyone is just trying to fend for themselves and solve problems and not spend a bunch of money. So it's a great place if you're 16 to 30 looking to break in the industry, kind of not expecting that major salary in the first year or two of us, of a startup, if you can provide real value, they will listen to you and they will hire you. But if you're just, oh, I'm a sports fan or I like sports betting or fantasy sports, there's a hundred, there's hundreds of those people, thousands of those people. You have to have more than that. All right. I love this. This is a fantastic strategy. So let's dig in a little deeper. So you're saying you've had people reach out to you, just slide into your LinkedIn DMs and say, I know you have this problem and I have a solution for it. Like that's how aggressive that they're approaching. It's not just like, I'm going to email in my resume. Like they're coming right at an issue and a solution. And that stood out to you. Is that right? There's one specific example that I remember a couple of years ago. We had grown a lot of prize picks that year, but our customer support was kind of like just getting overblown because we now had thousands and thousands of customers. We had only had hundreds of customers. We'd grown a lot in the last six months for a football season and had some good marketing spend going. And I got just kind of a DM from somebody. It's like, I work somewhere else in the industry. I can tell that y'all's support is overblown. I can fix it. This is how I'll fix it. Give me a chance. I love it. And we talked to him. We had a couple interviews and I was like, holy shit, this guy is going like, he means what he says. Yeah. He's pretty cocky that he's willing to write that and like, say, the problem and say that it's going to fix it. But he's confident and he has a solution and we brought him in and he's been one of the best, if not the best hire that we've made over the last couple of years here. So after seeing that, that formula I've just seen working. Sometimes you'll say that you have a problem and that might not actually be a problem and maybe it's not the right fit for you, but I've seen that work. I love that strategy and everybody listening, I don't think we're suggesting you go try to do that with the Boston Red Sox. But I think this strategy, when the startup culture makes a lot of sense of being aggressive and really stating, with confidence where you can help because that is what, if you reverse engineer this and you think of those of us that are employers, we have problems and the things we need solutions for and when we're hiring somebody, it's because somebody else left or we've identified something that needs to be solved. If you can be a problem solver, that is what we are looking for as a hiring class. So great, great, great advice there. Before we go much deeper into that side of things, I'd love to get your take on prize picks and what makes you guys different, better, whatever, however you want to articulate it in the DFS world and why you have so much pride in what you all are creating there. Yeah, prize picks has been awesome. I've been here almost six years now. It's been a really, really great ride to go. I saw on the ground level where we had 10 customers a night on the app and we were just getting off the ground and then we've built it into the beast that is today where I think right now I can put my phone probably number three in the App Store in sports. There's hundreds of thousands of followers on social media, players on the app, tweets, everything going around, there's lots of fun. So what prize picks is and what makes specials, so it's a pick MDFS style game right now that's a lot more that's going to be coming up in the future. But it's a really, really fun, fun game, casual friendly and really every decision that we've made across prize picks has been thinking about the casual sports fan first and what do they want to have in their experience. Again, I played Fandall and Draft Kings for a long time. It was great for me. I'm not necessarily a casual player. Like I said, I was spending eight to 12 hours a day on that category. So I'm not really the target customer. But we really just put a lot of work in figuring out what is fun for the casual, we built that game and built a brand, very, very thoughtfully marketing brand product all around that concept and from there, it's just really taken off and it's been a lot of fun to see it grow through all the ups and downs. Well, it sounds like you have a lot of partnerships too amongst the sports teams as well. So they're seeing the value in this product as well. And I've always felt like fantasy and some other betting and others, those bring in a lot of magic and understand why the pro teams want to align themselves because you're widening the fan base. And bringing in people who like the, you know, a different angle of it, rather than just the hardcore fan you're bringing in the casual fans. It's kind of like the whole thing going on right now with Travis Kelsey and Taylor Swift, right? Taylor Swift is bringing in a whole new set of eyes to Kansas City football games and NFL in general. It's the same kind of concept that daily fantasy, fantasy sports, all of this are bringing in more and more fans. One of those partnerships been like to know that you've got this approval stamp from, you know, some of these massive leagues like NASCAR and the Braves and others. So funny enough, we are the sponsor for Travis Kelsey's podcast, New Heights, and I didn't even know that. Yeah. So it's a great podcast. I mean, I like mine better, but there's this good. So we were checking this morning just on the, on how that show did in terms of conversions and CPMs and all those kind of things and they had an awesome day yesterday. So it's been really. I bet. You can also see what the Taylor Swift effect has on sports and on business as well. It's been really cool. But yeah, it's, we're looking for the Dylan Cooper effect on this show. Yeah. No, it might happen. You'll get like 200 years. Yeah. It's been, it's been awesome to work with the sports teams. We partnered with NASCAR, Braves, Falcons, Jaguars, Marlin, over the past couple of years, a bunch of other ones. Big three, American Corn Holy, and it's really, really great to have thoughtful partnerships with them where we're doing some kind of out of the box stuff that's creative, it fits our brand. And, and like you said, it's always awesome to have the stamp of approval of those big organizations. And it means a lot for social proof. Oh, for sure. It does. And just overall credibility. So let's talk about you. You're kind of career arc while at PriceBix. You've been there for six years. You guys have racked up a lot of awards. I was just looking really quickly that you guys won the Inc. 5000 America's fastest growing private companies. So it's back to back years in 2022 and 2023, fastest growing sports company. These are huge honors. These are really nice indicators of how successful you are as an organization. You personally started as an analyst, had a head of game operations. Now you see you oversee revenue. Now it feels like now you're lining up some of your Georgia Tech school, your classes that you didn't maybe put a amount of attention into your work life now, right? I mean, managing the revenue for a growing company like this that is on so many different fronts. How did you manage that transition? That seems like a pretty hefty leap from being diehard fan of DFS to now like Senior Director of Revenue. That's a big one. - Yeah, it has been a fun ride. I mean, I think a lot of it is, we started as a startup with three or four employees and I was, I was coming right out of school where I don't have any experience. So started off as an analyst. I think that's just kind of what, what I was qualified to do at the time. But I quickly, I think my passion for this industry and this knowledge of in and out, what works, what doesn't, what I had seen the past, quickly was recognized by Marceo and GoFounder Adam and TTO and GoFounder J, who have been awesome mentors and really allowed me with not as much experience as most people in this role to step up lead and take on more responsibility over the year. So I think really it's a testament to them of just trusting in me and allowing me to continue to step up and take on more and more. And what I've seen and what I really appreciate from them is as long as I perform as long as my departments perform, well, I keep getting recognized and moved up. And honestly, most of that praise goes to them for trusting in somebody where this is their first job, their first real full time job to take on those responsibilities and very confident that we're going to continue to successfully group prospects and execute it operationally well. And I appreciate their trust. - I'm a spoke in there too. I said senior director, senior VP of revenue. So I don't want to, I don't want to short your title there. So that's, that's always important to know. Senior VP of revenue, it's a big role. How much, you know, you think of those of us who are sports fans and I like you, grew up like spending so much time in the box scores and calculating data points and just seeing, trying to get little angles and conversations or whatever it could be, the DFS side of things. I'm sure you were pouring through data and really dedicated to that being a hardcore fan of this process. Again, being in the, on the revenue side of things for an organization, that also is some hardcore data manipulation. Do those two things overlap? Are they completely different worlds do you feel like of just that having that sense for the, for the data and the projections and how one thing influences another? Is that set the stage for you or is it, it's kind of different? - Yeah, so bring it up really interesting story. So when, when COVID hit, prize picks was around 30 employees at the time, but our revenue went away overnight. Our revenue was fantasy sports on sports games. So in the NBA, the NFL, all the sports, just overnight shut off. We ended up having to lay off basically the entire staff back in 2020, in March of 2020. And it came down to the two co-founders me and a couple of other employees that we kept around. We didn't take a salary for a little while there as we just cut back on our feet. But coming out of COVID, or before COVID, I was just in that game operations room, which means it's what you're saying. It's the projections, it's the trading of projections, modeling all the actual sports games. And that's what I was an expert with and that's what my main background was. But coming out of that, our team was very, very slashed. We didn't have the budget to afford a lot of the people that we had before. So Adam and Jay, one day called me and said, not only do you wanna do the projections, but would you also wanna own marketing? We think you have a good understanding of it. And then my first take was like, no, like I have to see the background, I didn't have a zero class on marketing in school. I have no idea where to start, but the response was, one, you know the customer as well as anyone, but two, it's just a math problem at the end of the day. And I had this idea of marketing is like, no, it's super creative, it's this and that, which today is I've learned over time that that is really, really true and you have to have both. But it's a lot more math and data analytics than you think. So coming out of that, I led marketing and almost handed over the projection side somebody else to run that was still on the team. And then over time, I've kind of merged the two into the revenue function, which overseas marketing, kind of like the operations of the game, operations of support, all those kind of things tied into one. - Yeah, it's a big challenge, good for you. So let's talk about that. Like when you're gonna start up, you are in a COVID era where things go down to almost zero, you're totally dependent on the games. Those aren't happening. You build back up and now you're in a, I would imagine a massive growth cycle. And so you can't ever really get content with where you are. You always have to be thinking about what's next. At least that's the way I would interpret from the outside. I imagine that's also your viewpoints. How do you continue to grow? How do you continue to stand out in this landscape, which is incredibly competitive? - Yeah, one more funny story I just had on COVID that I think is really cool to tell. So as I said, we laid everyone off. We had no supports in revenue. But first thing we did was try to figure out what supports could we offer? Is there anything going on? So one thing that we did do creatively was we partnered with the American Cornwall League. - Yeah. - They had matches on ESPN. They had people throwing Cornwall bags in their front lawns. And they had official scoring and tracking on it. And it was great. So that was one way that we were creative. And they've been awesome partners for us. They're still partnered with them today. - That's cool. - The other really cool one was esports. We had not really gone that far into esports. And that was the main thing that was so going. Like that was popping. That was like that blew up during that time. - Sure did. - So I actually went and said, I don't know esports. I don't know how to create projections for esports. So I literally went through Twitter and just scrolled through stuff. I asked some friends that might know people and ended up just Twitter DMing people that seemed like they knew esports and had some kind of a pulse in the fantasy world. - Yeah. - And we found a great person to run our esports during that time. But from there esports really launched off from price-bix is kind of a side thing. Turned into a main thing really fast. And now I think we're probably the biggest esports fantasy provider in the country. - That's super cool. So is that the big growth channel for you then? Do you continue to lean into that or are there other avenues that you start to look into? - Yeah. I mean esports is always a great growth channel. I think in general, there's just so much more green space. Like we've grown a lot, but it's a really casual friendly concept and just continuing to create more and more casual friendly games and concepts and channels for people to go. I think honestly using what's been tried to intrude as far as plenty more room for us to keep going. And I think if anything what we're looking for right now is potentially adding more fantasy games to the app where it would allow for more different options for players to show off their skill. - That's awesome. So as a senior VP of revenue, you have a team. You have a team of staff and you hire and you're probably influential as a leader within the entire organization cross-functionally. As you mentioned, a lot of different groups that you manage from marketing to customer support, et cetera. What are you looking for? When you're looking to start hiring people, when you're looking to expand and to grow, you're gonna get a lot of applicants. What stands out to you? What are those traits that you look for those skills that you look for to stand out in this world? - Yeah, I think it's changed over time. So when I was a startup, I was looking for who's gonna grind the hardest, who's going to who is really passionate about this thing and that formula worked over and over again. That might just be a specific bias of me, but that formula worked for so many hires, who is really, really laser focused passionate on this and gets the customer. That was the year one, two, three of those people will grind and work really hard to make this work. I think more recently as we've grown from true startup to we're transitioning from startup to more operational phase, probably right in that middle sweet spot right there. It's changed now, we are looking more for specialists of knowing sports or knowing this industry isn't good enough anymore. Now you've got to have some kind of expertise, like you're really good at paid social. Like if you're really good at that and you love sports and you love fantasy sports, that's a huge win. But stuff like that, stuff like offline media same thing. That was a hire that we just made in the last year. - That's a really good, buying TV spots. Or someone that's an expert on on trading and has experience working for other places trading projections like that somebody that in the past We were looking for somebody with some experience like now we're looking for more than the experts and the like specific vertical lane experts So over time it shifted towards that But I think if you don't have the experience you're you're your best Routes those early startups because we're truly looking for grinders that can solve Eight different things for us to not just have one vertical lane of expertise But if you're if you do have that lane or want to get to that lane, that's a great place to do a more experienced company It's great. It makes perfect sense Dylan, I'm so appreciative of your time. We'll finish up with this Many of those who's this show as I mentioned before tend to be in that 18 to 30-year-old range They're trying to start their career get their vision going for what they want for themselves as you kind of look back at your own Success and your own kind of growth pattern. It seems like there's this overarching principle of having a passion for something and following that Is that the suggestion you'd give to others who were listening or there's some other metrics you'd look at or some other processes you look at in order to To break into this industry and really find that niche and find that fit Yeah, that's it's it's a great question. It's it's a it's a hard thing because I think it's different for different people like Again, if you do have that vertical expertise in one specific thing whether it be analytics like that's a big place I think it's going to Explode and potential needs for jobs like we're hiring so much people that have analytics prowess can code Python SQL things like that We are working on some very ambitious projects that are taking years to work on that we need tons of people to help out there And I think that's just going to be the future of all this stuff So I'd say that that's a great thing where other vertical expertise is the way and if If not that if you're still in college or just out of college like look around at startups like maybe there's something that you can Give a startup most startups don't have a lot of money Yeah, and are looking for the shortcut where they can you can pay somebody a Lot cheaper than they would pay a an expert in the role some maybe that's where you find a solution is your Pretty good at something you're passionate about you'll work harder than anybody else and they aren't willing to pay up for an expert in that in that area So maybe you can fill in that gap and kind of grow into that role and grow into other roles in the organization We talk all the time on this show about having the skills in your in your toolkit that match up with industry demand And you just hit on it too if you want to work in this world and where the opportunities are and you're saying analytics and although I mean, it's like you said it Python sequel are you have to know those things so if this is something that interests you all the people in the audience You have to match the demands of the marketplace your skill set has to match those demands and if the audience can say I have these things that you need You're going to your resume is going to be taken a lot more seriously than just hiring somebody especially in your face right now Dylan Like before I get it you're taking those grinders those hard workers. We can train them. We can work with them as your growth cycle Increases then it becomes you need to be able to come in hit the ground running do a certain thing for us and then maybe expand another thing But you got to have that skill set first on so everybody listening Build up the skill set that matches the industry that you want the part of the industry that you want to go into Dylan This has been awesome Thank you so much for all this advice. Thanks for coming on and sharing more about price picks super enlightening And I know our audience will really benefit from it. It's not like one thing I wanted to add real quick was yeah Of the three languages that you mentioned there Python I strongly strongly suggest over the other two like I really really good at that one Sequel is also helpful, but that's the one that that we are looking we're going Python and I think in the industry in general It seems to be moving in that direction. So if you're in college looking to learn a language That's the one I would focus on there you go. That's awesome advice. Thank you so much Dylan great getting to meet you Thanks for coming on absolutely. I sure have me on so awesome Thank you Dylan for coming on the show. I always love topics and fantasy sports because I am terrible at them I have never been good at fantasy sports. I've always gone into leagues with people that don't work in the sports industry And there's an expectation. I'll do well and I stink It's kind of like the NCAA tournaments. So I don't know there's a whole different set of skills that go in there But the most important thing to pull from this for you is that's a lot of opportunities to work in the side of the industry too And it keeps growing and expanding and there's tech opportunities and there's analysis opportunities and their content opportunities There's a lot you can do in fantasy sports and it's a pretty cool industry part of the industry to grow alongside of Thanks for listening everybody. Thanks to Dylan for coming on and we'll see you all next week